Steve Jobs’ Customer Telepathy – How to get it – #4 in a series (~3 min read)

‘Get closer than ever to your customers. So close that you tell them what they need well before they realize it themselves.’ – Steve Jobs

I just heard a podcast where Joe Gebbia described that things really started to take off for his business when he got on a plane and sat with a number of customers in New York. He was able to see how they use the product, ask them why they chose it and what was most important to them.

Being a designer by trade, Gebbia is innately curious and has an unabiding thirst to learn. This steadfast curiosity helps him to be in the right frame of mind when talking to his customers. He is not trying to show them how to use his product correctly. He is not trying to correct their behavior. He wants to know what job they hired his product to do for them and how they employ his tool to get that job done. What need it fulfills for them and what actions they took to fulfill it. He is constantly searching for “WHY”.

It was after this trip that Joe said things really started to come together for him and his struggling company. It was not too soon after this trip to New York that Airbnb took off after years of hardship and toil. By getting to really understand its customers – their actions and needs – Airbnb turned the corner and soon after that fateful trip to New York become the largest hotel “chain” in the world.

This is the topic of the fourth in a series of startup to scale-up. How to prepare for and conduct the interview process. To quickly find out if your idea has legs or if should you scrap it and start on something new.

You may have a great idea but you are a bit early or you may think it is great but no one really cares. Your job is to create a viable business not just sell folks on your idea. The following are some ideas, tips and techniques to help you along the way.

Interview Process

A key component is the interview process with your target customer. The following are suggestions on how to manage the process.

Please note that from previous posts we have decided to move ahead with the idea and have nailed the pain and the target (or at least a hypothesis of what the pain and target are). We will now identify the interview process – the set of questions and the all-important mindset you need to nail to build your business.

Get Your Head Right

The most important part of any customer development interview is to be in the right frame of mind. Your goal is to learn about how your customer works and thinks versus proving that your idea is correct or nearly perfect. You need to put yourself in their shoes, you need to set your ego aside and let your empathetic side come forth. This is NOT about you. This is the best way to make your company successful.

The reason for setting your mind right is that during the interview process there is no set of questions that you can come up with that will work in every situation. it is impossible to anticipate every eventuality in this type of conversation. Each conversation will take on a life of its own so you are going to be making up questions on the fly based upon the answers/comments you hear. Therefore, how you approach the conversation is arguably more important than the questions you ask.

Sample questions

Before we go ahead and list questions that you ask your target customer, I recommend you ask yourself one question, “What am I trying to learn?”. You may want to learn if your target profile is right, maybe if your product features are important or possibly if you have the right business model. Keep your focus on the answer to this question to facilitate and expedite the process.

Now some basic questions from Lean Customer Development you can use the get the conversation going:

  • Tell me about how you do _________ today?
  • Do you use any [tools/ products/ apps/ tricks] to help you get ________ done?
  • If you could wave a magic wand and be able to do anything that you can’t do today, what would it be?
  • Don’t worry about whether it’s possible, just anything.
  • Last time you did ___________, what were you doing right before you got started?
  • Once you finished, what did you do afterward?
  • Is there anything else about _________ that I should have asked?

Quick aside

Every interview I have conducted (hundreds) and every book I have read (handful) that shows how to conduct this type of interview confirm that you should start with some questions to get the conversation flowing such as “How long have you been in this role?”, “How long have been with the company?, even talk about the weather, sports, something you see in their office or from their bio – whatever you are comfortable with.

Back to Interview Process

The interview will go off on many tangents as you work through the process. This is where getting your mind right is key so you can more deeply understand your customer’s needs and pains. You can mitigate getting sucked into the mink hole of proving how clever you are and if what you built or want to build is right. (Please note that a mink hole is a rat hole that feels good all the way down.) That comes later. Be patient as your patience will likely save you, your employees, investors, friends and family tons of time, frustration and money in the long run.

Have I spent enough time and ink stating how important your state of mind is going into these interviews? Ok, let’s move on.


Here is an oft-used example to prove the value of asking questions from the right frame of mind to learn about your customers and their true desires and actions.

If you ask someone what kinds of movies they like to go to, they are more likely to say 12 Years a Slave or The Piano or Schindler’s List, etc. However, if you ask them what movies they have gone to lately, the list is more often completely different such as The Avengers or Dumb and Dumber or some scary horror film.

The last set of movies more closely resembles who that person – actual vs. aspirational questions are important.

Asking questions to get to actual behavior gets you closer to the truth and will help you build a product that is much more likely to be one they will purchase and/or use as it addresses a real pain or need.

Avoid questions that have anything to do with you and your product. Ask open-ended questions as much as possible. Try to avoid questions that start with is, are, would and similar words that are close-ended and aspirational. They are not forbidden but you should avoid them as much as possible.

What to avoid

Here are some questions beginnings you should try to avoid

  •  How likely…..?
  •  How would…..?
  • What do you think…..?
  • Would you ever….?

The last thing to remember is, do not pitch or demo your idea until the interview process is over. Very important!

Additional Resources

If you would like some more in-depth guidance before you start, I recommend picking up Nail it then Scale It or Lean Customer Development. You can find a link to them on the Resources page on my site. I also show the 8-step process you can go through to get this right on my Offerings page.

Next time, we will talk about how you can start to nail the solution through the iterative prototyping process.

See you next time!

Be Exceptional! (;

I look forward to your comments. If you found this post useful, please share, comment and/or like.

Published by Bill Flynn

Gazelles Member Advisor and early stage startup specialist with a proven track record with 16 Boston-based startups (9 to date with 5 successful outcomes, advisor to 7 others); SMB to Fortune 500 companies. 20+ years of Senior Sales, Marketing and GM experience in industries including mobile advertising, security, digital advertising, e-commerce and IT. Core Competencies: Player/Coach, Metrics-driven, Execution-based philosophy, Life-long learner

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